


Lollipops and Pillows

by SabrielFluffFriday (Aria_Lerendeair)



Category: Supernatural
Genre: Awkward Flirting, Bad Pick-Up Lines, Canon Compliant, Episode: s02e15 Tall Tales, Lollipops, Love Confessions, M/M, Sabriel Fluff Friday
Language: English
Status: Completed
Published: 2016-12-22
Updated: 2016-12-22
Packaged: 2018-09-11 00:38:47
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 594
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8946031
Author URL: https://archiveofourown.org/users/Aria_Lerendeair/pseuds/SabrielFluffFriday
Summary: After Sam finds out that the sexy janitor he's been flirting with in Tall Tales is actually the Trickster he's been hunting, Gabriel leaves a lollipop on Sam's pillow.





	

**Author's Note:**

> [Prompt by Anonymous]
> 
> Sam using really insanely bad pick up lines on Gabriel during Tall Tales, because he thinks that's what the janitor would like, and then they agree to go on a date and Sam finds out Gabriel is the biggest romantic, and he goes away feeling giddy with happiness. Then they find out he's the trickster and Dean stabs him, so Sam thinks it's just another instance of the universe sucker punching him. But when they get to their motel that night there's a heart shaped lollipop on Sam's pillow.

OH GODDDDDDDDDDDDDDDDD, NOT BUT THIS IS ALTERNATIVELY SAD AND AWESOME AT THE SAME TIME, BECAUSE THE BAD PICKUP LINES AAAAAAAAAAND THE SAD.  

AND JUST.  OH GOD.  I HAVE SO MANY FEELS ABOUT THIS.  

Like, the date is probably the first time Sam starts to think that there might really be life after Jess.  That maybe, even if just for a night or two, he could find some happiness in a janitor that seems to like his terrible pickup lines, who has a wicked smile and who is secretly a romantic.  

(Sam sees how much he lights up when Sam buys him a rose and offers it to him….with another terrible pickup line.)  

And then Sam finds out everything, and he realizes the Trickster was playing him like a fucking fiddle and he’s angry and hurt and upset.  When he sees the piece of candy on the pillow, he hates how much his heart soars with hope.  

Then, several lifetimes (it feels like anyways), later, when Gabriel turns up again and Sam is worn down, he still can’t forget those stolen moments over dinner where it seemed like they were really…that they could have been something.  

So he avoids Gabriel, and tries not to let it bother him, but when the tension in the house starts to get palatable, Dean orders him to fix it, so Sam sits down and just blurts out to Gabriel was that night a game, was he just being toyed with, because he’d like to fucking forget it.  

Gabriel comes back with some sort of snappy comment about how he had no idea Sam was so gullible and then Gabriel watches Sam flinch, curl in on himself and get up to leave.  Normally Sam has much thicker skin and Gabriel is surprised, surprised enough that he pops into existence, his hands up in front of Sam, asking him to wait.  Sam only pushes around him and into his room.  

So Gabriel watches him go and chews on his lip and debates exactly what he should do.  So he pops a lollipop into existence next to Sam’s pillow.  And Sam picks it up, ready to chuck it in the trash when it crinkles.  He opens his palm and there’s a note attached to this one.  

He hates his traitorous heart for wanting to look at it, and he opens it.  

**_I’m a sucker for an awesome smile, bad pickup line and killer body.  While the chance to distract you was a welcome one - I was genuine after the first time I laughed._ **

Sam just stares at the note, and he hates himself for REMEMBERING the moment that Gabriel is talking about.  Gabriel had snorted and snickered plenty in the beginning.  But he had lit up and _laughed_ , really laughed, when Sam had told a story of some pranks that he and Dean had played in school.  

He swallowed and curled his hand around the candy a little tighter.  He unwraps the red sucker and pops it into his mouth before cringing and yanking it back out.  “Cherry, really?” 

“For your cherry ass!” Gabriel snarks from the other side of the door.    


Sam laughs and walks over to the door, opening it and saluting Gabriel with the candy, informing him that he’s more than a decade late with that candy.  

Gabriel just stares as Sam saunters back into the room and kinda whispers ‘ _Fuck me._ ’ 

Sam smirks and crosses his arms over his chest.  “Well if you insist, I’d be happy to oblige.”  

AND THEY LIVE HAPPILY EVER AFTER, OKAY?!

**Author's Note:**

> Originally posted at [aria-lerendeair.tumblr.com](http://aria-lerendeair.tumblr.com/post/121399239525/sam-using-really-insanely-bad-pick-up-lines-on) ♡ ♡


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